Homework Help: Organic Chemistry

Posted by Anonymous on Monday, October 1, 2012 at 2:29pm.

In lab, we did an oxidation of 2-ethyl-1, 3-hexanediol with acetic acid and sodium hydrochlorite. I understand the acid is the solvent and in combination with NaOCl produces hypochlorous acid the oxidizing agent. Then we mix with an ice salt mixture and then extract with ether before washing with sodium carbonate and sodium hydroxide. The part that confuses me is the washing. Both sodium carbonate and sodium hydroxide are neutralizers so why are both used? Wouldn't once suffice?

Organic Chemistry - DrBob222, Monday, October 1, 2012 at 3:32pm
Is the product an aldehyde or an acid? Which washing do you do first?
NaHCO3 is used generally to form the sodium salt of strong acid like carboxylic acids while NaOH forms salts with both strong and weak; i.e., phenols as well as carboxylic acids.
Organic Chemistry - Anonymous, Tuesday, October 2, 2012 at 6:12pm
The product was an ketone with the primary alcohol remaining. And the sodium carbonate was used to wash first then the sodium hydroxide.

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